Visible-Light-Induced Cysteine-Specific Bioconjugation: Biocompatible Thiol-Ene Click Chemistry.,Angewandte Chemie International Edition

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Visible-Light-Induced Cysteine-Specific Bioconjugation: Biocompatible Thiol-Ene Click Chemistry.
Angewandte Chemie International Edition ( IF 16.1 ) Pub Date : 2020-08-31 , DOI: 10.1002/anie.202010217
Hangyeol Choi _{1,

2} , Myojeong Kim _{1,

2} , Jaebong Jang ₂ , Sungwoo Hong _{1,

2}

Affiliation

Bioconjugation methods using visible‐light photocatalysis have emerged as powerful synthetic tools for the selective modification of biomolecules under mild reaction conditions. However, the number of photochemical transformations that allow successful protein bioconjugation is still limited because of the need for stringent reaction conditions. Herein, we report that a newly developed water‐compatible fluorescent photosensitizer Q_PEG can be used for visible‐light‐induced cysteine‐specific bioconjugation for the installation of Q_PEG by exploiting its intrinsic photosensitizing ability to activate the S−H bond of cysteine. The slightly modified Q_CAT enables the effective photocatalytic cysteine‐specific conjugation of biologically relevant groups. The superior reactivity and cysteine selectivity of this methodology was further corroborated by traceless bioconjugation with a series of complex peptides and proteins under biocompatible conditions.

中文翻译：

可见光诱导的半胱氨酸特异性生物共轭：生物相容性硫醇-烯点击化学。

使用可见光光催化的生物共轭方法已经成为在温和的反应条件下选择性修饰生物分子的强大合成工具。然而，由于需要严格的反应条件，使得成功进行蛋白质生物缀合的光化学转化的数目仍然受到限制。本文中，我们报道了一种新开发的与水相容的荧光光敏剂Q _PEG，可利用其固有的光敏能力激活半胱氨酸的S-H键，从而用于可见光诱导的半胱氨酸特异性生物缀合，以用于Q _PEG的安装。稍微修改的Q _CAT可以使生物学上相关的组有效地进行光催化的半胱氨酸特异性缀合。通过在生物相容性条件下与一系列复杂的肽和蛋白质进行无痕生物缀合，进一步证实了该方法的优异反应性和半胱氨酸选择性。

更新日期：2020-08-31

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